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I was a sore loser when I was younger. This is going to sound a bit geeky but when I was in 11th grade and playing a game of chess for the honour of my high school against the head of the chess team from a neighbouring school, I lost the game and was very upset about it. In one motion with my arm I knocked all the pieces to the floor.

It gets worse. I didn’t go back to school the next day or the day after that. I don’t even think I went back for the whole next week. It was a sickness.

I would hide outside until I could hear both my parents’ cars leave the driveway for work, then I’d take the bus into Princeton and meet John Nash to play some chess. Remember the film, A Beautiful Mind, about a brilliant economist (played eloquently by Russell Crowe) who then, very sadly, went crazy?

Well, this John Nash wasn’t him. It was his son. He had just received his PhD in mathematics and was very much like his father in a lot of ways. He was living at home and we’d get together and play chess when I cut school. He was a strong, master-level player who would tend to get nervous in tournaments and obsessively stroke his unkempt beard.

I couldn’t bear the thought of going back to school. In my mind I was labelled a loser even though nobody but me and my opponent really cared about the outcome of that game. But as human beings we tend to instinctively attempt to rank and label ourselves in some way. So when I was in high school I identified myself as a “strong chess player” and anything that got in the way of that made me feel less worthy of myself. You can imagine the number of girls who were attracted to me when I so labelled myself.

Much later, it wasn’t the number of chess games I won or lost that I used to establish my self-worth, but money gained or lost. There were only two situations I found myself in – “not having any money” and “not having enough money”. Neither is good.

Not having any money means a lack of freedom. While the desire for anything (including freedom) creates suffering, not having any money at all means you have to be enormously creative to get out from under the whims of those who have no creativity.

In spite of personal finance television shows, books and articles, the elusive “number” one needs remains just that. And it’s the quest for more that could trigger the conclusion of a life lived without consequence when lying on one’s deathbed.

This brings me to Britney Spears. I have never listened to her music. Nor have I seen her dance, including at the famous VMA awards (nor do I know what “VMA” stands for). I read Page 6, though, and follow her story and its very intimate details. Once I read a profile that suggested she was a brilliant businesswoman and manager of her own brand, a task she has let slide lately. But we can forgive her because she is 24 and we all remember what that was like.

I stood on Wall Street the other day doing a project for thestreet.com. I asked passers-by: “Britney, buy or sell?” and the most common answer was “sell”. So this young beautiful thing, this lost girl who sings “Gimme More” was consequential enough to inspire a flight of liquidity into – what? – more inspired personal brands?

When everyone says “sell”, we know it’s time to buy. This suggests some stocks.

Skechers – Britney is a celebrity endorser for Skechers footwear and I’m personally excited about their “Cali gear” line, which is similar to Crocs.

Jakks Pacific makes a Britney doll. The company trades for less than five times earnings before interest, taxes, depreciation and amortisation and will have a strong run into Christmas on the heels of the problems facing Mattel.

Elizabeth Arden makes a Britney fragrance as well as perfumes for other celebrities. At 10 times ebitda and with analysts steadily upping estimates, I think the company is poised for an upside surprise at its next earnings report. I would place the bet now, since it’s relatively safe at this multiple.

Pepsi – Britney is a celebrity endorser for Pepsi. Sugared water doesn’t go out of fashion in a recession. And with a 2 per cent dividend and growing foreign sales, it’s hard to find a safer bet.

And, of course, Sony, which puts out Britney’s single “Gimme More”. With 100 per cent earnings growth over the past year, I think this will be the ringleader of the Britney snapback rally.

When I wake up, the twin demons of fear of loss and angst over self-worth try to guide my day. And every now and then I still knock over the chess pieces when I lose. But if I’d never done that I wouldn’t have had any material for this fantastic column – if I say so myself.